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After receiving an investment offer at the $1 billion, I came back to a board meeting and suddenly one of the directors stood up, took out a piece of paper and said, I'm calling vote of summoning the CEO to a pre dismissal hearing. A startup is more like a marathon because 90 to 95% of the time I'm in crisis mode, depression mode. This is the reality and this is what we sign up for. Just like when we go running, we sweat. Same as in this journey.
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Ranan Cohen, serial entrepreneur, started and was CEO of two startups. One had an ipo, one was a unicorn. Now in this fascinating book, Confession of a Unicorn founder, he literally pulls back the curtain on their darker side of entrepreneurship.
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Entrepreneurs and managers, usually there are people who are used to success and suddenly when you go on this journey, you start to receive no's, you start to get ghosted from investors. And this is a shock. And what I like to say, you know, if you're going on this journey, it's okay. This is the game.
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How do you cope with rejections and challenges and hard moments?
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Never take strategic actions when you're suffering. Move on, finish this pain part and then make the decision now you're living
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a great life, but if you know where that next 15 years have been, would you still jump to entrepreneurship?
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It comes with a lot of pain. The problem is startups.
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Welcome to the Leap Academy with Ilana Golan show. I'm so glad you're here. In the Leap Academy podcast, I get to speak to the biggest leaders of our time about their career, how they got where they are today, the challenges, the failures and countless lessons. And so lean in. This episode is going to be amazing. I'm on a mission to help millions reinvent their career and leap into their full potential land their dream roles, fast track to leadership, jump to entrepreneurship or build portfolio careers. This is what we do in our Leap Academy programs for individuals and teams. And with this podcast, we can give this career blueprint for free to tens of millions. So please help my mission by sharing this with every single person you know. So because this show has the power to change countless of lives. Dio. Okay, so let's dive in. Okay, so here is a story for you. I always make a point to check if a podcast guest has a book and if they do, I listen to a few chapters as part of the prep. Right? So a few weeks ago I'm going hiking on the weekend and I start listening to this book from my next guest. The name of the book, Confession of a Unicorn Founder now listen to this. I had so many things I needed to do and listen to that day, but I just couldn't stop listening to this. And it all resonated so, so much. By far one of the best books I read in a long, long, long time. And it just takes you on this emotional journey that you will not forget. Ranan Cohen, serial entrepreneur, started and was CEO of two startups. One had an ipo, one was a unicorn. Now in this fascinating book, confession of a unicorn founder, he literally pulls back the curtain on the darker side of entrepreneurship on startups on the venture world. Listen, I am warning you, you will not want to put the book down and and you will have to listen all the way to the entire episode. So get ready to see the world of entrepreneurship in a completely different way. Also remember at the end of the conversation, I choose a question you wrote on our YouTube channel. So today, inspired by this conversation, we'll answer a question about dealing with rejections in the hard moments. So let's go. Ranan, so good to see you on the Leaf Academy show.
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Great to be here.
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Oh this is going to be so fun. Plus we share a birthday. What are the odds? So cool. January 25th, do you remember? Yeah.
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January 25th.
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Let's go. So happy birthday to you.
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Sort of that I know that was born on the same day I was. So yeah, it's a first for me.
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Woohoo. So I do want to start a little bit from actually the end. Why write such a book and what are like some of the biggest false beliefs maybe that you wanted to break with this kind of a book?
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After my over almost 15 years of a CEO and founder of startups, after the second one is a pretty sudden exit without any spoilers. I didn't have any retention or any time that usually happens after a founder's exit. So I took it as a project and went to Bali for one month to brainstorm what I'm going to do with the other half of my life. And at the top of the list was I want to write the story, I want to write my experience. I felt I remember myself coming into this world of startups, entrepreneurships. I had a totally different perception. We are living today in the startup world and I think in general in a culture of fake it till you make it, which is great manifestation and everything. I believe in it. But the other side, the flip coin of this is that coming into the world you can get a real shock by starting to feel how it really is. And I felt strong passion to write about it initially I planned to write it for myself, friends, for colleagues and just give it away. It wasn't planned to be a commercial book. It contains sensitive stuff about the tech ecosystem and then some venture capitalists and others. Obviously I changed names, but it was also a story how it rolled out into a publisher, the leading publisher in Israel. And it was released just over a year ago and surprisingly for me, it became like a national bestseller and now it's going international and now I'm also working with a production film and doing a TV series. So it opened a new life for me and I get feedback on daily basis from entrepreneurs, founders or people who are curious about this world. And it's super exciting for me.
B
Oh, this is so fun. So I'm not the only groupie here that love the book, but let's take you back in time then tell them a little bit of the story. So first of all, you do talk about having imposter syndrome where you got into tech. Take us back in time a little bit to those early days.
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I didn't come out of any flashy tech, military unit, AD200 or others. I was a combat soldier and officer. And after that I worked for the prime minister office. And then I found myself studying accounting. Four years of boredom, soul crushing grind. And as I was about to turn 30 years old and start my internship at KPMG, just like all the big things in my life by chance, I received a phone call from a friend who asked me, hey bro, you want to work in a startup? And I said, what are you talking about? So he said, yeah, listen, you traveled around the world, we're looking for someone who knows other cultures. And you've been an officer. And we need a project manager, someone to communicate between the local engineers and the international customers. You get free food and a gym membership. And I said, I'm in. So I called my parents and said, hey mom, there's not going to be a CPA in the family. And I started a junior role at a startup. It was back early 2000 in the mobile space. The mobile industry was exploding back then and there were dozens, even hundreds of startups. And this was one of the hottest startups in the Israeli tech system. I was very fortunate to fall on this startup by chance that has an amazing founding team, founders, and they were not only very highly talented, but they were also great humans. From day one, I had an imposter syndrome. I remember coming into the startup, I was introduced to my team manager. She was 24, super talented. And I said to myself, okay, in this lifetime, I probably missed it. I played around with other stuff and I'm coming in too late to the game. But they were super kind and I learned everything on the job. In retrospect, all the seeds that flourished later on were planted being in this amazing startup. So the imposter syndrome followed me from day one. I felt that any minute someone would knock on my door, say, hey man, you're cool, but you don't really fit in. And this together with some idea that I have about roaming phone calls, it was some kind of vague ideas. The two forces came together and at the age of 34, I resigned my role and told my CEO, Hey, I'm going to build my own startup and
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take me there for a second, Ranan, because at this point, you're not the typical kid selling lemonade. So why a startup of your own? That is a really scary thing. Was it scary for you where you're just mainly excited? Where was that?
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Now with the reflection. I must admit that people ask me, how did you have the courage? Back then, I was already married. Our twin Girls were like 2 years old and the mortgage, you know, the entire deal. And people ask me, where did you have the courage to live a great job with nice salary? And to be frank, I didn't have the courage. I had a brother of courage. Sometimes you can bring the brother in. And this brother was, I have nothing to lose. I mean, I was sure that it's just a matter of time, very short time, until my bluff is cold. And so I have nothing to lose. So when you have nothing to lose, you can already go for it. So until today, I play with the thought, what would have happened if I would have felt secure and thriving in my job? I'm not sure I would have made the jump. By the way, today when I mentor entrepreneurs and I lecture and I tell them about this, sometimes there is like a misconception that a founder, when he's on the start line, he's like Superman, I'm going to conquer the world. I know what I'm doing. I have it all figured out. Let's go and do it. I tell them, no, you know, this is not how it works. We go to the start line and there are many black holes, butterflies in our stomachs, so many questions, and we jump into the water in spite of all these. And you never get them all figured out and everything in line.
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And let me ask you for a second Anand before we continue with the story now, in retrospect, and again now, you're living A great life. But if you know where that next 15 years have been, would you still jump to entrepreneurship? Because I think sometimes we also jump because we're ignorant. I can say that for me, my ego, running some pretty good organizations, like I felt like, oh, I got this, this is going to be a piece of cake. And it wasn't. So would you in retrospect, jump or no?
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I wish I would. Because you know, there's something beautiful in my eyes in naiveness or, or the ignorance of at least the first time founder. You don't really grasp the journey you're taking on yourself. You're not really aware of all the pain and suffering. It's really helpful, almost mandatory in order to make this step because like for my kids, someone asked me, did you wish your kids will be founders, entrepreneurs? And frankly, no. The only thing I wish for them is to be happy. But if I would have recommended going into a direction, it comes with a lot of pain and it's great that I didn't know about it.
B
So take us to the first time that you're trying to raise capital. You always talk about selling the dreams and it's true. Like in entrepreneurship, you constantly need to sell the dreams to everyone, including yourself. That's what motivates you. So talk to us a little bit about that, just starting with your company, Mobile Max.
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So as a startup founder, I mean the first thing is raising capital. And also I was very fortunate. Again, this relates to the thing we just talked about that I had no clue that I have zero chance of raising money. I mean back then the ecosystem wasn't that sophisticated. They were like VCs and the founders, but there wasn't all the ecosystem support. And coming without tech education, without a fancy military unit, without any medal to show, raising money from VCs, your chances are almost zero. I didn't know that back then. VCs, venture capitalists, they like to invest in serial entrepreneurs, IPO unicorns, or in someone that the entire industry is chasing. And all the rest need to find a way to squeeze out some pennies. But I had a lucky break. My lucky break was that two VPs from the startup that I worked in, the CFO and the CMO, David and Israel, which I didn't work directly with, but they knew me being a small startup of a few dozens of employees. And they approached me and said, hey Ronan, we heard you're building a startup. We want to be your first checks. We want to invest each 30, $40,000. You know, we like you, you're A hard worker and we want to put in the first money. Now, back then I didn't realize what a life changing event that was because in addition to the working capital that I could start using, I used this while pitching to other angel investors. Again, this is in retrospect and when I talked with them after the book was released, they told me, yeah, you didn't have the cv, you didn't have the experience, you didn't have anything. But these guys, they were NASDAQ veterans, they already been through a successful ipo. And the fact they put in money and together with the fact that they worked with you for three years, so they know you pretty well, this gave us the comfort to put the money and I raised a million dollars and suddenly I have a company. Mobile Max. Terrible name, right? But that's what I had available back then with Mobile. Mobile Max, software platform for telecom carriers. You know, in startups, just like in surfing, sometimes it's not just about how good of a surfer you are, it's about what day did you catch and what day did you go into the water. And we are like mid 2000. And all the stars aligned. The mobile industry was booming and multiple devices, a jungle of devices. Nokia, BlackBerry, Samsung, lg. And what turned out that our platform that had the capability of enabling, developing once and deploying it on multiple devices, back then, the devices were not compatible, so it was a nightmare for development of applications. So this capability that we had was gold for the telecom carriers and it was gold for the developers. And we started signing up telecom carriers all around the world at&T, Verizon, Telefonica, Vodafone. It was just one after the other. All the stars aligned and it was
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exploding and you go public, which is incredible.
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Yeah. So less than three years after founding the company, underwriters came knocking on my door saying, hey, we've been following Mobile Max, you're perfect for an ipo. And we went public and suddenly, you know, zooming out a bit, ran. And the guy who sneaked into the tech industry just trying to hold on to my job and building a startup because I had nothing else to do. And suddenly I'm a CEO of a public company. I'm on the press, I'm talking to analysts, I'm on stages. This is wild. I was in like my early 30s. So things like that, that happens when you manage to conquer one dream after the other. This is amazing. It builds what I believe is the most important muscle in our body, which is the muscle to believe that you can do Anything. Now this has also a dark side. This muscle. This muscle says, okay, I'm unstoppable. No one can stop me. I know better than everyone, at least for me. At my early 30s, I became a little cocky. I had the sports car and you know, you feel like a rock star. It's crazy. So luckily, I don't think it had effect on my personal life and personal interactions, but on the business. Just after we went public a few months later, they were one of the institutional investors called me and said, hi, Ronan, we have our investments manager on the line. We want to buy from you shares at $10 million. This is only a part of your shares now. This is 2007. Back then, $10 million were a lot of money. Even today, $10 million is a lot of money. Especially for a young guy with kids and mortgage and family. And I found myself telling them, hey, I appreciate the offer, but the company is just at $100 million now. We're still growing, we're going to be billions. Selling now would be losing money. I gave this speech and they said, okay, are you done? We are familiar with the CEO's speech, whatever, it's very emotional, but we all know how it ends. Say I do and the money is wired to your bank. That's the beauty of a public company. No negotiations. You just get the money and celebrate. Now, back then, today, I want to believe that I'm not that triggered and that I would respond differently. But back then what I heard is that you're just playing us. You don't have the balls not to sell. You're going to sell. And when I heard someone thinking like that, I was just more luck. And I'm telling them, listen, you're wasting your time. We're not going to talk about it before it hits a billion. And that's how the call ended. And they tried to insist. They called our accountants, ey and our lawyers and to convince me and I was the more cause I was more locked in. And this passed. And a few months later, the black swan of the mobile world, iPhone was launched and started to gain traction. And then came his brother Android and suddenly an entire industry that was multiple devices jungle, basically our entire value proposition. It took a few years, but it became worthless. So that was the implication of my smart decision not to sell.
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We need to pause for a super brief break and while we do, take a moment and share this episode with every single person who may be inspired by this because this information can truly change your life and theirs. Now I want to check in with you. Yes, you are you driven, but maybe feeling stuck in your career or a fraction of who you know you could be, do you secretly feel you should have been further along you in your income, influence or impact? Do you ever wonder how to create not just a paycheck but the life you want with a paycheck? The thought leadership, the legacy, the freedom. Because that was me. And that's exactly why I created the Leap Academy program, which already changed thousands of careers and lives. Look, getting intentional and strategic with your career is now more important than ever. The skills for success have changed. Aq, adaptability, reinventing and leaping are today the most important skills for the future of work. Building portfolio careers, multiple streams of income and ventures are no longer a nice to have. It's a must have. But no one is teaching this except for us in Leap Academy. So if you want more from your career in Life, go to leapacademy.com training check out this completely free training about ways to fast track your career and and you'll even be able to book a completely free strategy call with my team. That's leapacademy.com training too many people finish their workday feeling frustrated, drained and unfulfilled. The good news is it doesn't have to be that way, and you don't need necessarily a new job to fix it. Patrick Lenteoni, author of the Five Dysfunctions of a Team and more than a dozen other bestsellers, created the Working Genius assessment to help you pinpoint the kind of work that gives you energy and the kind that drains it. Over a million people, including myself, have taken it, and it completely changed how I lead and how I show up every day. So if you're a CEO or entrepreneur or someone who just wants to level up in business and in life, working genius will give you the clarity and the confidence to operate in your strength and really find greater joy in what you do. Because confidence isn't about pretending that you're good at everything. It's about knowing where you're truly gifted. So take the Working Genius assessment today. Get 20% off with the code LEAP@workinggenius.com that's workinggenius.com you'll be glad you did. At that point, you need to admit that this thing is collapsing and you didn't take the money. And even though to some extent it looks like you did an IPO and you're probably a millionaire because that's how we look at people. Now you're trying to figure out how on earth am I doing the everyday Work, because I don't even have a job, right? Like I need to just maintain myself. Take me through that. And you talk about it in such a beautiful way in the book. But take us a little bit that time between the two startups. What was it like for you and for your family, honestly?
A
So I'm already like 40 years old, we have four kids, still mortgage the entire package. Mobile Max was an eight year adventure. Lots of fun, lots of experience, nice cool T shirts, but not a cent in my bank out of this journey. So this obviously has implications because going into the startup game, we know the statistics, we know the statistics are against us as founders and most of them don't make it. And it's okay. For me, there was another level to this. I managed to step on the podium. When you do an ipo, you're on the podium. There's the price, the investors can sell, you can take the money. And instead of doing that, I placed all the money back on the roulette table and gambled like my family's financial future. So there's a lot of conscience. So this was a period, a very, very complicated period for me. Sleepless nights with Ravit, my wife, you know, so I kind of like toned it down. I said, you know, don't worry, I'm going to build another one, don't worry about it. I had no idea what I was going to do. I just tried to come up with ideas, crazy things like dating apps for 70 year olds, diet over gambling, any idea I could think of. And the problem is with startups, I talk about when I meet people outside the industry, if you're an entrepreneur in, let's say, normal industries, if you are in real estate and you build buildings, so you did one, you have the playbook, and now you're going to do another one. Obviously there's uncertainties and there are surprises, but there is a playbook. And eventually this project you're going to put in a few years and something is going to turn out. There is a route to the middle. In the startup world, you're aiming for a moving target and there's so many moving parameters. The technology, the industry, the customers. So the chances, the fact you did it, okay, you get a lot of experience, but winning the lottery again is a totally different game. And that's how I felt. I felt like, okay, I blew up my lucky chance and now I'm just trying stuff that doesn't work. And it took a while. It took like almost a year of trying and obviously economic implications on the Family issues with the partner. You don't see the light at the end of the tunnel. And back then it seemed like almost hopeless. Until again, by chance, one night. So every Friday night, like we have a pizza night. One night the pizza was late again. With four young kids and a wife, a late pizza can be drama, even big drama. And this was a night of big drama. I said, okay, I must look into this. Now we are talking like just over 10 years ago, 2013. So we had Amazon prime taking off. We had Uber. There were like advanced services, but not as it's popular today. E Commerce was like 5% of retail. Today it's over 20%. It was gaining a lot of traction. And what hit me is I said, okay, when I order a pizza, why can't I have the same experience when I order an Uber or Amazon? Why can't I see it and communicate with it and everything could be smooth? And then looking into it, the answer floated pretty fast. That when ordering pizza or a package or a technician, all these companies, they are not tech companies. And unlike Amazon or Uber or the new guys, they don't have the capabilities to develop these advanced delivery and logistics functions. And this planted the idea that if I could develop a software platform that would enable these old school, the Fortune 1000, the old guys, the same capabilities that Amazon and Uber developed for themselves, this would be great. There was one main problem. I'm not a techie guy. I don't know how to develop it and I don't know if you can develop it and how to approach it. But I love sports and I love marathons. And in one of the marathons I met Lior, Lior Sion. He was back then the CTO of Get Taxi Gettaxi, Israel's Uber. So it's like the number one candidate to talk with him about this. We were just like Facebook friends. And I DMed him and said, hey, let's have coffee. And from the first minute this idea sparked and we understood that what these companies developed internally, this would be a mandatory requirement for anyone who delivers. And we got together and founded bring. So bring is a SaaS software as a service company that enables companies that have deliveries, these advanced logistics, capabilities of optimization and customer facing, et cetera. And the company from day one exploded. I mean, we signed up customers all around the world, huge brands like Walmart, McDonald's, Pizza Hut, all around the world, 50 countries.
B
But before that, before it explodes, you talk a little bit about also raising capital. And even though it's like a second time et Cetera, it was still hard. So can you take us there for a second? Because I think there's also a myth that, like you said, if you've done it once, it's gonna be so easy on the second time, but it's not necessarily. You're gonna have your own ups and downs, even though it's a second time.
A
Yeah. Raising money in general, you know, it's tough. So this time I came to it in a strategic manner. And I remember my previous times, I said, okay, this time I want to come like a rock star. So what does that mean? So I defined a checklist of what would be rock star status for a startup like mine, meaning we have design partners, we have customers, we have web360. All the parameters that if I would face an investor, it would stand out. I mean, VCs see like 1500 startups a year. They invest in five. This will be one of the top five. Together with Leo, we defined what we need in order to accomplish this rock star window. And we worked back from that for nine months. We were in stealth mode. We didn't approach any Investor. And with VCs and investors, you know, today I'm also an investor. We always like to say as investors, you know, you can come even early on when you're not ready, because we always want the foot in the door, we want the option, we want to know what's going on. This is like a small trap because they said you only have one chance to make a first impression. And there's like the next door's neighbor's son syndrome. So if you come in too early, they label you. And today everything is in the CRM and you're labeled. You can turn it around, but it's pretty tough, so it's better. And this is how it works for us. For nine months, we're still small, didn't talk to investors. Once we felt we were strong and ready, we came out. And again in one month, we received investment proposals from the top VCs, Sequoia, Blumberg and others. So it was a totally different strategy. We were also, as the founding team, two founders, one experienced after ipo, the other one like national tech leader. So the team was also set in place. By the way, initially, I was very concerned about the way Mobile Max ended. After eight years, it crashed to zero. So I was concerned and what I found and learned, and today it looks pretty straightforward to me, that this journey was perceived as a very strong, unique capability. So the fact that the technology changed, you know, iPhone and Android came in the entire industry shifted. These things happen. And I'm mentioning this because today I talk to a lot of entrepreneurs that want to go to a second time, and they're very concerned about the outcome of their first journey. This was a very, very surprisingly good lesson to understand coming after a first round, if you did the journey, you built a team, you scaled it, you raised the money. This is super valuable. So we went out and started funding, and from there it exploded. And again, the stars aligned beautifully because Amazon was killing it. And initially we had very nice decks and presentations explaining why fast delivery and efficient delivery is super important. And all our customers said, hey, we don't need to see these decks. We know this better than you do. Amazon is killing us. Show us what you can do for us and let's talk business. So this was a dream come true. And we scaled the company, signed up customers, and raised like $200 million every three months. We had an inbound round doubling or tripling the valuation. It was like, crazy, crazy. And this time I learned. Not every time I learned from my mistakes, but this time I learned. And from a certain point, every investment round, I sold some shares. My co founder, Leo, also sold some shares, Also some employees. I insisted that employees will sell some options. And the more funding we got, the more shares we sold.
B
But somehow the investors didn't like that.
A
Yes, yes. So investors, in this context, you can define them in two types. Ones who believe that it's great that founders and employees will stay with the backs against the wall, no dollar in the bank, they will be hungry. If they will cash some money, it will reduce their motivation. There are some that believe like that. There are others that believe on the other side that if you along the journey. And again, assuming this is a successful journey, it's not a. The company is collapsing and you're running away. The journey is successful and you manage to get some money along the way. This is good for everyone because this will increase your dreams. This is the capitalistic lifestyle that we are living today. This hedonic treadmill that we're running on, for good or for bad. I'm running on this treadmill. There's always something that I crave for. And I almost swear to the universe, just get me this. I just want this, this promotion, this money, this whatever. And I swear I will never ask for anything again. And then we get it.
B
And the carrot moves again.
A
Of course. Yeah. If you dream of closing your mortgage, then you'll dream of your house. And you get the house you want. Houses for the kids, and then you want planes. And it never ends. So the modern investors understand that and they also, they even encourage founders and employees to cash along the way. In my journey, I had the other types, the old schools, and they didn't like it and they told me they didn't like it, they didn't like me selling shares. But the eight year scar was still stinging my back.
B
You're like, I'm not doing this mistake again.
A
Yes. I said, yeah. I used to tell them, listen, I understand you're not comfortable with this, but I have a family, I have a wife, my priorities are different. And eventually this led to the first page of my book where I came back from after closing our biggest deal ever, like a $40 million deal, after receiving an investment offer at the $1 billion, I came back to a board meeting, I landed to a board meeting. I had champagne set up and I was sure, you know, there's nothing like a big win to clean the air in the locker room. I was sure, okay, this will clean everything. All the nonsense that we thought about and I'm going to get medals. And I was walking into this board meeting and sharing the news of our big deal and our big investment. And suddenly in the middle of my presentation, one of the directors stood up, took out a piece of paper and said, I'm calling to vote of summoning the CEO to a pre dismissal hearing. And that's how the book starts. So apparently they really didn't like all the share selling. In retrospect, I don't think it was about selling the shares. It was more, I think, about ego. So investors, VCs, many of them don't really like when a young founder, they tell him do this and he does otherwise. And then he does it again and again and again. So it's not really about the cash out. I think it was more about ego. And then World War 3, half of the book is about that. Between the VCs and then 2021 when the company hit unicorn, the billion dollar valuation. I sold my shares, retired, and wrote the book. And surprisingly since then, almost on a weekly basis, I get messages from readers telling me, hey, you wrote our story. We had similar stuff. Usually these stories end with an NDA and the founder on his knees and needing to go back to the industry so it doesn't come out. So I get a lot of these. So now I'm in my third startup. The book, the TV series, the lecturing. It's a new life for me.
B
I've been in some of the startup ecosystem and some of these meetings and meetups and everybody's feeling like a superstar and there's this whole fake it till you make it. And then on the other hand, we toss and turn in the middle of the night and nobody wants to admit it. Right? How does that play that consistent? This is where I need to fake it. But on the other hand, I can barely breathe and everything is collapsing under me or in both of the companies, like when it actually happened.
A
So this was one of the main, I think, triggers that pushed me to write the story because, you know, today in the startup world, and I think in general, we're living in this fake it till you make it culture because, you know, you need to manifest success to create success. It's a great attitude. But again, this comes with a cost. So I remember myself doing this year after Mobile Max, before bringing, I used to go to investors meetups and startup events. And I remember, you know, just before stepping in the door, I used to take a deep breath and meditate to put in a million dollar smile because I was the guy everyone was pointing at saying, hey, he just did millions after an ipo and now he's doing another round for fun. And you know, you walk in the events and for those who are not familiar, you know, there are like baristas and bartenders and the worlds that are flying in the air are like fabulous, killing it, exciting. And everyone seems so successful. And there's also in the media and in the social media, there's this very strong winners bias, right? Every day we see this one did an ipo, this one sold another round. We don't see the other 99 or 999. So I like to use the analogy of sports and running marathons or ultra marathons. So when you're running for a marathon, training for a marathon, there's a famous phenomenon called the wall that after three hours, it's like your body has no glycogen and you feel like you can't go on.
B
Some of us, it happened before the three hours. I'm just saying
A
it can happen much earlier. Yes. And everyone that trains for it knows about it. And I remember myself in my first marathon in Miami marathon, I hit the wall. It was crazy. It's like you feel you can't move on. And I remember after one second I said, hey, here it is, the famous wall. And I kind of even smiled to myself, hey, okay, I'm facing it. This is what I signed up for. And then I recall that everyone tells you, okay, you just need to Carry on. Even if you slow down a bit, just continue and it will pass. And you continue, you go on and life goes back to normal and you go in and you head to the finish line. So in the startup life, in the startup journey, no one tells you about these walls, and these walls are multiple walls. So, you know, there's a misconception. People talk about startups, even myself, as a roller coaster, right? But when you think about it, roller coasters, 50% of the time go up, 50% of the time go down, right? This is physics in a startup. It's more like a marathon, because 90 to 95% of the time I'm in crisis mode, depression mode, I'm sure that it's going nowhere. And maybe there's 5% of smiles and high. And the problem is that if we are not aware of this, I mean, deeply aware of this, this could lead to very problematic decisions. Such as I was sure during this time that one of the two. Either that I don't fit this founder character because it looks like everyone is. Is having a great time and everyone is so relaxed and successful. And I'm not sleeping at night, so maybe it's not for me, or that I may be thinking that I'm not on the right path because it shouldn't be like that. This is something I talk about a lot in universities. This is the reality and this is what we sign up for. Just like when we go running, we sweat and we start sweating and we know this is how it is with running, same as in this journey. And the problem is that if in a marathon, you have a training plan, right, for a few months, you train and you increase your mileage and it's very difficult. But if you stick to the training plan, to the gameplay, there are high chances that you will reach the finish line and get the medal. The problem with the startup journey is that you never know if there is a finish line on the path you're going. There is no playbook. And when things are really tough, when you're in misery in a marathon, I fantasize about the medal and the finish line. And I said, okay, I just need to push through and I'll get it. In startups, you think I like the sentence, you know, not all pain is gain. You think, maybe I'm going nowhere, I'm just suffering.
B
But that's so depressing. How do you continue, Ranan?
A
It's depressing, but this is the game and, you know, it's all about. I believe in general, in life, it's about framing. If I'm facing a hill now and I'm going to run a hill, I know that my quads are going to burn. So when they burn, I said, okay, this is it. And when you're going on this founder's journey and you deeply understand that your muscles will burn. And I remember at Brink Brink was my second round, so I came more mature. And when we had some tough days, I used to grab Liora and we're going to the office, and I used to smile and say, hey, man, this is so fun. It's like Monopoly. Now we are facing this world that seems unsolvable, and people gave us money to solve it. This is. And he used to say, you know, you need to calm down with your meditations. But I think we need to adopt this kind of mindset in order to not only survive, you know, we want to strive because it's a long journey and we need to find our own tactics to go along the way. I use also sports a lot, but I think understanding and realizing that this is the misery I'm going through, it's not a problem I should have avoided. This is the reality that I need to face. And there will be good days and bad days, and this is what I signed up for. And everyone is suffering. Everyone around me has the same pain, and it's okay.
B
I think this is such an important message, Anand. And it's funny because when I need to summarize the entire Leap Academy podcast in one word, it's probably grit and tenacity, because that's what all the leaders, if you actually listen to everybody like you and some of the biggest leaders, like Tom, Bill, you said, don't ask me what's the least I can do. Ask what's the maximum you can bear, right? And it's like it's really more about what can you take on. But you do talk a lot about your crazy runs. And this is not just marathon. These, like ultra running is like a very different beast than marathons. And I did one Ironman and never going to happen again. But tell me a little bit. What are some of the things that running taught you? Or how do you see the similarities and why on earth to run ultra marathons like you did? Tell me.
A
I use this mantra that there is a quote in the first page of the book, a quote from John Rockefeller, the first billionaire in the world. He was asked once casually in a conference, how much is enough? His answer was, just a little bit more. So this. Just a little bit more. This is a mantra that I love very much. And it has different meanings depending on the context. But in running, for example, I'm a late bloomer in everything. My first marathon was at the age of 38. I gave myself a birthday present. It was a disaster. I barely finished, I barely walked after that. But I signed up for another one immediately after. And a year later a friend called me and said, hey, there is like this thing called the triathlon. Do you want to do. There is an ironman where iron you swim and then you bike and you do a marathon in the end. So I went into that and then you're in this network of people and someone says, hey, there is a ultramarathon. You know, it's. I was sure that after, you know, a marathon, the world ends after the marathon, right? 26.2, that's it. Suddenly there is a 50 mile race and I signed up for that. And then again people around you talk about and by the way, this is has I think also it's a great example about the people you surround yourself for good or for bad. And when you surround yourself with like lunatics and the Saturday night someone asks you who's up for a 40 mile run tomorrow? And it sounds normal. So you started doing that. And 100 miles is like the holy grail of ultramarathons. They're even longer ones than that. I did a few of these and what I found amazing is that doing these runs, you know, especially in parallel to the being a startup founder, CEO, it's like meditations. You detach the agony of the body takes you to a very, very deep place. It's magic. I rolled into this direction, especially after I sold my sports car. I got rid of it and I didn't have a car and I started running to the office and I found this new cheat system of instead of driving, running to the office and back. And this became my lifestyle. So I got free mileage on expense of commute. And this became a part of me. And I remember that in our lives, every morning I used to wake up this monkey mind and the million things and a million worries. And I put my running shoes on and I used to go out and as the miles go, suddenly the water that was very, very wavy comes down and things are clearer and the problems don't disappear, but everything looks less dramatic. And it's like it gives me a special pill to carry on for another day. So this was like my mental detox. And then I highly encourage you know, adopting something I remember I used I run along the beach And I used to look at fishermen, you know, sitting there for hours with. And I didn't get it. Today I get it. It doesn't matter what. But if you have a hobby you're passionate about that distracts your mind from your daily grind. This is magic. It's just one step after the other, just a little bit more, and you find yourself doing these long, long runs.
B
Yeah, I have a feeling that some of us will not find themselves doing these very, very long runs. But I. Kidding. But I think there's also a quote that I love from you that you say something along the lines of never make race decisions on an uphill. And I think that was also just such a good. Because sometimes we're in a rut and everything looks bad. And if we're going to make decisions from that wall or from that uphill or from that really hard moment, that's clearly going to be a bad decision.
A
Yes, that's totally another side of this mantra of just a little bit more. So I have, like, a rule with myself that every time I'm facing, like, a very tough decision with the startup or in life or in the relationship or anything, and I want to quit, I have this rule where I say, you know what? Okay, but let's continue just a little bit more. And in the ultra world, there is this mantra of never make race decisions on an uphill, which practically means never take strategic actions when you're suffering. Move on, finish this pain part, and then make the decision. And like in life, you continue doing this uphill and you finish the hill, and suddenly it's not that bad. You can carry on. And it goes along, by the way, with another ultramarathon meme which says, beware of the chair. Right. So, you know, if you're in pain, you're tired, you're burned out, it's okay to take it slower. It's okay. But don't stop. Because if you stop, you know, that's it. You never know what cramps can jump on you and things that happen. So it's okay. You know, you can't run a marathon in one sprint. It's okay to slow down, but don't stop.
B
I've done my races. I don't know if I could ever go back to it, but it is incredible. Like, my team knows that if I don't go and at least hike or run every single day, I get annoying. I am not myself. But when you kind of look at yourself and you're kind of in a third phase, if you will, or Whatever that is. How did your definition of success change
A
Ranan Today for me, success, I look at it as I have several buckets. It's not only one bucket that I need them to be as full as possible. So there is family, there's financials, there's health, there is meaning there are a few buckets and I need all of them to be at an optimum level because you know, let's say if just health is bad then all the rest are meaningless and same with other, if your relationship is bad then that. So I need all of them to be as high as possible and it's different than in investments, right? So today if I invest in five startups and only one of them makes it big time, this is a great success. But for me today I need all these handful of buckets in an optimum level. And today building a startup is like doing ultramarathons. Today I do marathons. I don't do ultramarathons anymore because ultramarathons, like startups, you need to be all in. In a startup, a founder is all in and people talk about work, life, balance. You can close the laptop and you can take vacations. And that's what I used to do. But I used to play with my kids at the beach, but my head was somewhere else. As a founder of a super intense venture, this is a price that we pay. And if you're a founder, you're all in. Just like if you're doing ultra marathons, then you can surf and ski and yoga because you're either running or you're recovering. That's the two stages. So today I think, and by the way, there were bets on me that after bring I would build another one. I wouldn't last three months, six months. I told them no more.
B
You're having a great time, I can see it.
A
Yes. And I was very fortunate to find at the late stage a new passion which was writing and the impact and the world that it opened for me. And I think that entrepreneurs, and by the way, when I say entrepreneurs or founders, it doesn't mean you're a startup founder or a business founder. You can be in a founder or entrepreneur state of mind or state of living as a school teacher, as a public employee. In every one of my companies I had multiple entrepreneurs. And in my definition, living as an entrepreneur means three things. One is that you're living with passion, right? You're not just coming along, you're with passion. Two, you take 100% accountability. I'm responsible, it's about me I'm going to make it happen. And three, you're proactive. In my definition, if you have these three ingredients, you're an entrepreneur. The framework can be startups, can be business, can be civil servant, can be in different ways. So in this life of being an entrepreneur and being a passion, it comes again with the fact that you're all in.
B
And I love that because it's true. You can't really turn full entrepreneurship off at any given moment. Like, I think it's very, very hard. And I do believe a lot of people, even if there are executives or in a company in corporate, they will start creating more portfolio careers we kind of talked about. So they will have many side hustles and things that they're doing either for passion or for income or for reputation or for fun, or they will have multiple ventures. And I think we're seeing a world where everything is shifting. So everybody will need to have that passion, ownership, proactiveness, all the things that you talked about. But what is. When you look at entrepreneur and you, I know you mentor a lot of entrepreneurs now, what was probably some of the biggest things that you want them to hear now? Or maybe some of the people listening to this and they're debating, like, should I jump to something new? How do I decide what's next? Like, what are some of the things that you wish somebody told you?
A
I like to carry the torch that anyone can, and I'm an example to it. I didn't come with the background or the fancy Ivy League. And again, if you would have told me the age of 30 or even 34 before I started my first company, that I would be a CEO or a founder, I didn't have it in my books. I wasn't the kid who sold lemonade at the corner or had any of these. He won't point out. I truly believe that you can build yourself and educate yourself and inspire yourself to a journey that will lead you this way. And today, the possibilities even grew. So I was very fortunate to find myself in a startup where I was inspired by amazing founders. It was truly luck. Today we can do that not only on the physical level, we can do it also on the digital level. So the feeds that I have on social media, workshops that I go to, online courses I can surround, podcasts, books, whatever. I can surround myself with a soul, nourishing content that could take me and anyone that is curious. You need to do the work right, you need to put the time and you need to put the energy. But if you will do that, you can turn yourself into an entrepreneur, a founder. And I remember myself looking at CEOs on stages or reading books and I used to tell myself, you know, I can see he has it, this guy has it. I will never be able to do what he does. And later on when I was on these stages and behind the curtains and talk to the CEO, you can see they're all normal people. You can build yourself toward this. You need to put in the work. But today there's endless possibilities to do that. Another thing that I like to wave at is that I am a very late bloomer in everything. In marathons, in writing books, in starting. My first grown up job was at 30, right? My first startup was at 34. So you can start at any time, you can make a change at any time. And again, I was lucky that I made this jump where I felt that I was pushed to it. Today it's very tough because these questions, I get these questions on a daily basis. You know, I'm not sure, should I leave my job, should I try? Should I? In many cases, I think we're over dramaticizing the price of the decision or the cost of the decision. Because for example, when I worked for this startup and I said, okay, I'm going to found my own, what was the worst that could happen? Let's say it would crash. I wouldn't be able to raise funding, I would need to look for a new job. Okay, it may take me six months, a year, it's painful, but it won't kill me. And on the other hand, the upside is very big. And another thing we need to remember, you would never feel ready. You would never feel ready. These kind of changes and journeys, we need to understand that we fill the gaps as we go along and we never feel ready. And I think that the last point that I like to emphasize, and especially, you know, entrepreneurs and managers, usually there are people who are used to success. Success we're using to get a plow. In our childhood, at school, we're always the ones who succeed. And suddenly when you go on this journey, you start to receive no's, you start to get ghosted from investors. And this is a shock. And what I like to say, you know, if you're going on this journey, it will be tough. It will be tough, you know, you will doubt yourself and it will be tough, but it's okay. This is the game, everyone goes through it. Just come into this game understanding that this is how it goes, you'll get through it.
B
This is incredible. Let me do one more Thing that usually I don't do with guests, but if you have a few minutes, I would love to. So every week we get questions on our YouTube channel and usually I just answer it. But I think because you talked about it right now, like I have to get you to answer it. So Trish asked about how do you cope with rejections and challenges and hard moments. And I will add also, how do you also create a little bit of a layer, of a thicker skin? So let's answer it together for Trish. I think that's going to be really, really fun. So I'll get you to start. Ranan, how do you deal with those rejection, with those hard moments? Because you started, I have to get you to finish this.
A
I turn to my religion. My religion is sports, right? So I like to look at it. You know, when a basketball player goes on court and he misses a shot, you don't see him catch his head and say, wow, I need to retire. I missed the shot. Right? I think this is a healthy way to look at this stuff because we are doing hard things and we're going on court and we are sometimes trying to make these shots from half court and when I'm shooting from half court and I miss one after the other after the other, when we look at basketball, we say it makes sense, it's okay, just keep on shooting and eventually you'll get the one in. And that's how I look at life and look at these situations when it's part of the game. I just need to continue and increase my options for luck and have this kind of mindset because again, the grit part, it's not only about surviving. We want to survive and still have the spark. It's not like surviving like someone who is about to drown in the ocean. We want to survive but with a smile and with the spark and understand. I'm going to keep shooting until it will come in and then I'm going to get the trophy.
B
Oh my God. I love your answer, Ranan and I will give my answer after we drop. I don't want to take your time but thank you for making this so, so fun and inspiring and amazing as I knew it would be. And for everybody, just go get the book and where can they find you,
A
Ranan on social media, anywhere. And ranankoin.com the book is on Amazon, audible and I'm very accessible. I'll be happy to hear from everyone.
B
Go get it. Confession of a Unicorn founder trust me, you will not regret it and I can't wait to actually hear your comments on the show because you will love it. So thank you so much, Anand. You are the best. And I can't wait to go running with you sometime in like, maybe jogging, doing something.
A
Absolutely. Had a great time. Thanks, Ilana.
B
Okay. I hope you enjoyed this episode as much as I did. This conversation is so, so good. Seriously, that book is wow. But Trish, you asked an incredible question about rejections and challenges, and I wanted to give you a little bit of the way I see this. So again, the hard things about rejections is that you forget all the great things that you've accomplished and you start believing the rejection, the hardship, the things that are hard. And what I want to do is give you very practical tools that I use in order to continuously remind myself that I can do this, I can do big things. So that's what we're going to talk about. So first of all, thank you for the great questions. If you have more questions, put it in the comments on our YouTube channel and we going to look for them and we're going to pick a question and we going to answer them every week. So the very first thing is to remind yourself that success leaves clues. And all you need to do is remind yourself of those clues, right? So number one is just write down all the little things that made you successful in life. And it's interesting how again, when we're down, it's hard to even remember. But I want you to take a look deep. Even as a kid, as a teenager, in college, whatever, like all the little things that made you successful, maybe as a parent, maybe as a kid, as like, what made you successful. And think about all the skills, all the things that you accomplished, all the places where you got awards, all the places where people say thank you. Thank you. So think of all these moments and write them down. The second thing that I want you to then do and again, take five minutes for each one of these. So turn off notifications and again, write down everything, all the places where you've been successful, number one. Number two is write down what are you grateful for right now? And what's beautiful is it is like when we're really down, sometimes we can't even feel. Feel that we're grateful for anything. But if we actually force ourselves to look, I mean, I can breathe, I can see. The trees are beautiful, the sky are blue, whatever, right? Like there's still things that you can be grateful for right now. So try to find the little moments that make you feel grateful and write them down again. Just take five minutes don't take it long, but really kind of force yourself to think about the little things that make you grateful. That roof over your head, whatever it is, food on the table, et cetera. So the little things. But really remind yourself that there's reason to be grateful for whatever you have right now. Number three, what I want you to write down is who you'll be in the future. And the way I want you to write it is I am basically a really badass whatever, like business person and I'm creating these big things and I going to be successful because 1, 2, 3, all of these things. And I want you to write this down and I want you to remember who you are, the badass person that you are. You've been successful at all these things. You're grateful for all this and that's what's going to make you successful. And with that state of mind again, if you do all these three things, it's only going to take you about 15, 20 minutes and you already going to feel like the badass person that you're meant to be. So I hope you're gonna win big time. Trish. Let us know how it worked in the comments. All of you, if you heard this and this has helped you or if it didn't help you, let us know in the comments and we're here to support you and can't wait to see you win again. Share this episode with everybody you know. Click the like subscribe, download all the buttons because it really, really helps us continue to bring amazing guests and to Kinu to make this show even better. So lots of love to all of you and let's go crash the day. Bye everybody. Remember, this episode is not just for you and me. You never know whose life you meant to change by sharing this episode with them. And if you love today's episode, please click the subscribe or Download button for the show and give it a five star review. This really means the world. Join me in helping tens of millions of individuals reinvent their career and leap into their full potential. Look, getting intentional and strategic with your career is now more important than ever. The skills for success have changed. AQ adaptability, reinventing and leaping are today the most important skills for the future of work. Building portfolio careers, multiple streams of income and ventures are no longer a nice to have. It's a must have. But no one is teaching this except for us in Leap Academy. So if you want more from your career in Life, go to leapacademy.com training check out our completely free training about ways to fast track your career. You'll even be able to book a completely free career strategy call with my team. So go to leapacademy.com training.
Episode: The Dark Truth About Venture Capital: Confessions of a Unicorn Founder | Ra'anan Cohen | E155
Date: April 23, 2026
Guest: Ra'anan Cohen (Serial entrepreneur, author of "Confession of a Unicorn Founder")
Host: Ilana Golan
In this candid and revealing episode, Ilana Golan hosts unicorn founder Ra’anan Cohen to discuss the often-overlooked dark realities of entrepreneurship and venture capital. Drawing from Ra’anan’s bestselling book, the conversation pulls back the curtain on founder struggles, boardroom power dynamics, imposter syndrome, founder mental health, and what it really takes to survive and thrive as an entrepreneur. The episode is rich with powerful stories, actionable lessons, and practical advice for anyone thinking about leaping into startups or reinventing their career.
“A startup is more like a marathon because 90 to 95% of the time I'm in crisis mode, depression mode. This is the reality and this is what we sign up for. Just like when we go running, we sweat. Same as in this journey.” – Ra'anan Cohen (00:00, 37:13)
“You never get them all figured out and everything in line.” – Ra'anan Cohen (09:31)
“There’s a winner’s bias... we don’t see the other 99 or 999.” – Ra'anan Cohen (35:33)
“Never take strategic actions when you’re suffering. Move on, finish this pain part, and then make the decision.”
– Ra'anan Cohen (01:11, 46:18)
“If you think about marathons, you train, you know you’ll reach the finish. In startups, you never know if there even is a finish line.”
– Ra'anan Cohen (38:28)
“You would never feel ready… We fill the gaps as we go along.”
– Ra'anan Cohen (51:50)
How to cope with rejection and tough moments?
“My religion is sports… when a basketball player goes on the court and misses a shot, you don’t see him catch his head and say, wow, I need to retire. I think this is a healthy way to look at this stuff… just keep on shooting and eventually you’ll get one in.”
– Ra'anan Cohen (56:25)
This episode stands out for its searing honesty and practical wisdom. Ra’anan’s journey—from unlikely founder, to IPO, to unicorn, to public boardroom ejection—illuminates crucial realities hiding behind the “success theater” of startup culture. Anyone considering their next leap, especially towards entrepreneurship, will find essential lessons in resilience, humility, and creating meaning across all areas of life.
For further insights, check out Ra’anan’s book “Confession of a Unicorn Founder” (available on Amazon & Audible) and connect with him on social media or ranankoin.com.